Working with a boss who has never had an assistant before

Working for a new Executive who has never had an assistant before can be a tricky situation to find yourself. You may have been an assistant for years and know the role inside out, but your new Executive doesn’t have a clue what you do and how to work with you. In this instance assistants really do have to take the lead. It can be time consuming and frustrating, particularly if you are also working with an number of other Executive’s or if you have been given this new Executive without much notice. But it is worthwhile. You do have to work together and you will have to prove to them what you can do. You may also have to push back if they don’t have a very good perception of assistants and treat you like the office dog’s body. Here are my top twelve tips for assistants who are working with a boss who has never had an assistant before.

Delegation: Your new Executive will need to learn to delegate work to you, which will be new to them. A great way to start is by showing them what you do for your other Executives or what you have done in the past. Make a list (or use your job spec if it is update and relevant) of everything that you are capable of doing. They may not need you to do everything but at least they will understand how much you can actually help them.

Get the basics up and running straight away: Tell them you will need access to their inbox and calendar. This is nonnegotiable from your point of view. You can not effectively assist them without being able to manage their schedule and review their emails.

Set boundaries: It is really important that you set boundaries early in your working relationship so that you both know what is expected of you. Clarify the different tasks you will be completing for your Executive and if you are comfortable with them. Although they are new to having an assistant you are not new to the role so you can have some say over what you do.

1-2-1 meetings: Ideally you want to see your new Executive a few times a day but ensure you have a 1-2-1 meeting with them at least once a day. Schedule this in their diary straight away. The sooner they get used to how closely you will work together the better. Write the first agenda for this meeting and make sure the first point of conversation is on the structure of your 1-2-1 meetings.

Priorities and objectives: You will need to quickly understand what your Executive’s priorities are for the coming months and their objectives for the year. Your Executive will also need to know your priorities, especially if you are an assistant to more than one Executive. It is also really important that you share your career development plans with your new Executive so that they know you take your career seriously.

Over the first few weeks take the time to work out your new Executive’s ‘work style’. How do they work, how do they communicate and what does their routine look like. This will help you be proactive in your new role.

An Executive should be able to trust their assistant but this is easier said than done. It certainly makes the role much easier. So do, from the outset, be enthusiastic, open and honest with your new Executive. The sooner they realise they can trust you with confidential matters and complex tasks the easier it is to work together.

Get to know them: Do try to find a common ground and show friendliness and respect towards your Executive. You don’t have to be friends but it can be easier to establish a comfortable working relationship when you add a personal touch. If they are receptive go out for lunch every so often and take your catch up meetings outside to a coffee shop at least once a week. This will give you the opportunity to meet in a relaxed atmosphere and get to know each other a bit better. Having even a basic knowledge of your manager’s home life is beneficial in building a good rapport with them.

Learn how your Executive prefers to communicate. Some Execs like to have frequent face-to-face meetings, while others prefer e-mail or phone check-ins. Your manager might like to get frequent updates on a project, or he might want to be informed only if there is a problem. Pay attention to your Exec’s communication style and ask what communications method they prefers if you are unsure. This way, when you do need to talk about something important, you will be heard.

Keep your Executive in the loop: Continual dialogue provides the opportunity to gauge progress, make sure you are on the right track and adjust your actions accordingly. If needed you can ask for additional resource or change any deadlines. By keeping your Exec in the loop you will ensure they are aware of your progress, good or bad.

With long term tasks, such as diary or email management define exactly how they want you to manage their correspondence and calendar. Again have this conversation immediately – how else do you know if you are meeting their expectations?

Do be patient with your new Executive. We all have to learn new ways of working on taking on a new assistant can be daunting especially if your Executive is new to the role and has loads of other aspects of their job that they need to learn. They may be overwhelmed and really this is where you can help.